Snapchat CEO Evan Spiegel makes a living with a product that erases our embarrassing moments, yet he can't seem to shake his own embarrassing past.

The 23-year-old Spiegel, who made headlines in January when emails he sent to Facebook CEO Mark Zuckerberg were made public, is in hot water once again for old email messages — and these are difficult to justify.

Valleywagpublished a collection of emails that Spiegel sent as a fraternity brother at Stanford University's Kappa Sigma house, many of which refer to excessive drinking while Spiegel was underage and crude sex jokes. He refers to sorority girls as "sororisluts," and in one email even jokes about peeing on a sorority girl from the university.

This was one of the more mild lines from an email:

Our pledge class is currently dominating the f*ck out of everything and if I hear one more freshman tell me how much they love kappa sigma ill probably get so excited ill punch them in the face.

The emails, which appear to be from the end of Spiegel's freshman year and into his sophomore year, were sent out to a fraternity pledge class email list. Spiegel released a statement through a spokesperson to Mashable regarding the emails: "I'm obviously mortified and embarrassed that my idiotic emails during my fraternity days were made public. I have no excuse. I'm sorry I wrote them at the time and I was jerk to have written them. They in no way reflect who I am today or my views towards women."

Spiegel has battled the perception of immaturity in the media before, and emails like this won't help his case. It's more bad press for a CEO who keeps overshadowing his product. After a public dispute with Forbes in January, multiple investors told Mashable that Spiegel's behavior as a CEO didn't matter as much as the company's product.

"Every VC I know is like, ‘F*ck, I wish I was in Snapchat,'" one investor told us.

Of course, you can't hide behind a great product forever. We assume Spiegel wishes he could make his emails disappear, too.

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